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Art. -Nr.: HY-N19651

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Oxophoebine

Oxophoebine is a biologically active oxoaporphine alkaloid and also a DNA topoisomerase inhibitor. Oxophoebine acts as a cytotoxic agent against certain cancer cells. Oxophoebine binds to Measles Virus fusion protein, hemagglutinin and phosphoprotein, and interferes with viral entry, replication and particle assembly processes. Oxophoebine exhibits selective toxicity towards yeast mutants with defects in DNA repair and recombination. Oxophoebine can be used in studies related to measles and coronavirus disease 2019 (COVID-19).

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CAS. Nr.: 109175-37-3
Formel: C₂₀H₁₅NO₆
Molecular Weight:365.34

Speicherung:

Please store the product under the recommended conditions in the Certificate of Analysis.

Oxophoebine Chemical Structure

CAS. Nr.: 109175-37-3

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Classifications
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Biologische Aktivität

Beschreibung

Alle Topoisomerase Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
RAW264.7	IC₅₀	34.2 μM Compound: 14	Antiinflammatory activity in mouse RAW264.7 assessed as inhibition of LPS-induced NO production preincubated for 30 mins followed by LPS stimulation measured after 24 hrs by Griess reagent based assay Antiinflammatory activity in mouse RAW264.7 assessed as inhibition of LPS-induced NO production preincubated for 30 mins followed by LPS stimulation measured after 24 hrs by Griess reagent based assay	[PMID: 33939429]

In Vitro

Oxophoebine does not exhibit significant cytotoxicity against human breast adenocarcinoma MCF7 cells, human nasopharynx carcinoma KB cells, or human small cell lung cancer NCI-H187 cells, with IC₅₀ values >50 μM for all three cell lines^[1].
Oxophoebine (100 ns) binds with high affinity to FUP, HMG, and PSP with MM/GBSA binding free energies ranging from −40.68 to −25.37 kcal/mol, exhibits favorable pharmacokinetic properties, and acts as a promising multi-target scaffold for anti-measles virus inhibitor development^[2].
Oxophoebine binds to SARS-CoV-2 M_pro with a binding affinity of -7.6 kcal/mol, forming multiple non-covalent interactions with key protease residues^[4].
Oxophoebine (48 h) shows selective toxicity against DNA repair and recombination-deficient Saccharomyces cerevisiae strains (rad 52, rad 52.top 1, rad 6) with IC₁₂ values of 6.4 μg/mL, 2.6 μg/mL, and 4.7 μg/mL respectively, while being inactive against the wild-type rad⁺ strain (IC₁₂ >500 μg/mL)^[3].
Oxophoebine is present as a major constituent in the broad-spectrum antibacterial fractionated extract of Annona squamosa leaves, but its direct antibacterial activity is not demonstrated^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Chemical Information

CAS. Nr. 109175-37-3
Molecular Weight 365.34
Formel C₂₀H₁₅NO₆
SMILES

O=C1C2=NC=CC3=C(C(OC)=C(C(C4=C1C=C5OCOC5=C4)=C23)OC)OC
Structure Classification
- Alkaloids
- Quinoline Alkaloids
Initial Source
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

Please store the product under the recommended conditions in the Certificate of Analysis.

Reinheit & Dokumentation

Handling Instructions (2659 KB)

Verweise

[1]. Rayanil KO, et al. The first total syntheses of (±)-norphoebine, dehydrophoebine, oxophoebine, dehydrocrebanine, oxocrebanine and uthongine and their cytotoxicity against three human cancer cell lines. Journal of Asian natural products research. 2016 Nov;18(11):1042-56. [Content Brief]

[2]. Oloche JJ, et al. Molecular Modeling Identification of Key Secondary Metabolites from Xylopia aethiopica as Promising Therapeutics Targeting Essential Measles Viral Proteins. Evid Based Complement Alternat Med. 2023 Feb 9;2023:1575358. [Content Brief]

[3]. Harrigan GG, et al. Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea. Journal of natural products. 1994 Jan;57(1):68-73. [Content Brief]

[4]. Ogunyemi BT, et al. In-silico investigation of oxoaporphine alkaloids of Xylopia aethiopica against SARS-COV-2 main protease. AROC in Natural Products Research. 2022;2(1):01-12.

[5]. Dholvitayakhun A, et al. Potential applications for Annona squamosa leaf extract in the treatment and prevention of foodborne bacterial disease. Natural product communications. 2013 Mar;8(3):385-8. [Content Brief]

Calculators

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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MOQ

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100 mg

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